Ammonia → HCID 71625874, compound

HRID 589606Notes

Reaction equation

HRID 589606 reaction equation
ClC1C=C(SC2C3C(=CC(C)=CC=3)[NH:12]C=2CCC(N)=O)C=C(Cl)C=1.[Cl:25][C:26]1[CH:27]=[C:28]([S:33][C:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[NH:36][C:35]=2[CH2:44][CH2:45][CH2:46][C:47]([OH:49])=O)[CH:29]=[C:30]([Cl:32])[CH:31]=1.C(Cl)(=O)C(Cl)=O.N>>[Cl:32][C:30]1[CH:29]=[C:28]([S:33][C:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[NH:36][C:35]=2[CH2:44][CH2:45][CH2:46][C:47]([NH2:12])=[O:49])[CH:27]=[C:26]([Cl:25])[CH:31]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 71625745HCID 71625745, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625874HCID 71625874, compoundYield 17%

Procedure

Following the method used to prepare 24a, the use of 50 (135 mg, 0.34 mmol) and oxalyl chloride (43 μL, 0.51 mmol) followed by reacting the intermediate acid chloride with aqueous ammonia (2 mL) provided 23 mg (17%) of product 24c as a pale yellow solid, mp 163-164° C. 1H NMR (300 MHz, CDCl3) δ 1.92-2.01 (q, J=7 Hz, 2H), 2.25 (t, J=7 Hz, 2H), 2.46 (s, 3H), 2.96 (t, J=7 Hz, 2H), 5.42 (brs, 2H), 6.84 (d, J=2 Hz, 2H), 6.96-7.00 (m, 2H), 7.21 (s, 1H), 7.38 (d, J=8 Hz, 1H), 9.34 (brs, 1H). LC-MS (CI): m/z 393.0, 395.0 [(M+H)+ C19H18Cl2N2OS requires 392.05]. Purity (100%). Calcd for C19H18Cl2N2OS: C, 58.02; H, 4.61; N, 7.12; S, 8.15; Cl, 18.03. Found: C, 58.06; H, 4.79; N, 6.88; S, 7.90; Cl, 17.75. The low yield for amide preparation in this case was due to the significant formation of a six membered lactam via cyclization of the intermediate acid chloride.

Sources & evidence

ORD record
ord-450d4bf8dd664c89a1d8a2538a27ac88
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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